Stereospecific Synthesis of Functionalized Cyclopentane Derivatives

Abstract

A general method for the stereospecific synthesis of 2, 3-trans-3, 4-cis-trisubstituted cyclopentanones (9) is described. This synthetic method has the advantage that three functional groups can be stereospecifically introduced on a five-membered ring by the catalytic hydrogenation of 2, 3, 4-trisubstituted cyclopentenones. Furthermore, 9 could be stereospecifically converted to 1, 2-trans-2, 3-trans-3, 4-cis-trisubstituted cyclopentanols (20) and 3, 4-cis-disubstituted cyclopentanones (11) by a simple procedure. These synthetic methods may be useful for the synthesis of natural products containing a five-membered ring.